Jessie Gill

Jessie Gill is a seasoned senior executive and strategic operations leader with 16 years of experience serving in Chief of Staff roles across complex, high-growth organizations. She currently serves as Senior Vice President and Chief of Staff at Wheels, LLC, a leading fleet management company, where she partners directly with the CEO to drive enterprise-wide strategy, long-range planning, and transformation initiatives. In this capacity, she leads the organization’s strategic planning process, ensures alignment across business units, and provides executive oversight that translates vision into measurable, cross-functional outcomes. In her day-to-day leadership, Jessie oversees the execution of key strategic initiatives while maintaining enterprise accountability across priorities. Her responsibilities include executive decision support, governance coordination, and high-level operational execution. She routinely prepares in-depth CEO briefings covering client, market, and geopolitical context, and participates in executive forums where she may represent leadership in decision-making discussions. Her work reflects a Chief of Staff model aligned with senior executive operations, serving as a central connector between strategy, leadership priorities, and organizational performance. Jessie began her career in executive leadership in 2010 at an energy efficiency SaaS company, where she was first introduced to the Chief of Staff function and mentored into the strategic discipline that would define her career. She has since held leadership roles across industries including fleet management, Am Law 100 legal services, and global consumer brands such as Dunkin’ Brands and Arby’s Restaurant Group. Across these environments, she has built a reputation for operational rigor, discretion, and strategic clarity. She is also the founder of JKG Elite Consulting, where she provides fractional executive advisory services to CEOs and organizations navigating growth and transformation, drawing on a career-long commitment to executive partnership and organizational effectiveness. Beyond her professional work, Jessie enjoys international travel, spending time with family, and music. She frequently travels with her mother and plans several major trips each year, including recent visits to Thailand and Amsterdam. She is also a musician, playing saxophone and keyboard in support of her fiancé’s music career, reflecting a creative balance alongside her executive leadership responsibilities.